When Was the Last Time You Followed the Rules?

Not all the rules we followed were necessary

I interview a lot of candidates for roles at my office. The other day, I was paired with a colleague I hadn’t interviewed with before, and she asked a question that caught my attention:

“When was the last time you broke the rules?”

For me, the more interesting question might be: “When was the last time you followed them?”

It’s probably not surprising that someone who writes a newsletter called 40 and Giving Zero F’s has a complicated relationship with rules. I’ve always been inclined to question them — bend them when possible, break them when necessary.

I tend to gravitate toward activities that reward creativity and improvisation rather than strict rule-following. Cooking, for example. I love to cook. I hate to bake. Baking requires precision and restraint — two qualities I possess in… limited quantities.

(For the record, some of my favorite people are bakers.)

In fact, I can pinpoint the last time I followed the rules without really questioning them — and realized later that it didn’t serve me. I was in third grade, and it was time to choose a musical instrument.

I desperately wanted to play the violin. But musical talent does not run in my family, and my mother gently steered me toward band instruments instead. String instruments, after all, are notoriously difficult to learn. (And tend to sound like a dying cat while you’re figuring them out.)

There was a form to fill out: list your top three instrument choices. The only ones I actually wanted were flute and clarinet (like most eight-year-old girls). But the form required three.

So, with absolutely no understanding of what it was — this was pre-Google, after all — I wrote down French horn. It sounded elegant. It was French. It had to be beautiful.

Well, of course, I was assigned the French horn.

Since no one else wanted to play it, the school generously offered me a free rental — a very smelly, dented, thoroughly abused instrument that I was suddenly expected to practice at home. As soon as I brought it through the front door and attempted my first notes, my father promptly nicknamed it the “fart horn.”

You can imagine how that went.

I stuck it out for the year. But instead of quitting music altogether, I made a plan.

I tracked down the string teacher, figured out how much it would cost to rent a violin for the summer, and priced out private lessons. Then I presented a budget to my parents and proposed a deal: I would try the violin for one summer. If I hated it, didn’t practice, or turned out to be terrible, I would quit at the end of the season.

Spoiler: I didn’t quit. I was actually pretty good — and I kept playing until college.

Looking back, I doubt that form actually required three choices. Two probably would have been just fine.

But I followed the instructions anyway — and spent a year playing an instrument I never really wanted.

It makes me wonder: how much of our lives is shaped by unnecessary compliance? By rules we assume we have to follow, even when we don’t?

Some rules absolutely exist for a reason. This is why my chocolate chip cookies never turn out as well as my husband’s — he follows the recipe and I… interpret it.

But plenty of rules are just silly. Or outdated. Or things we’ve accepted without ever really questioning. By midlife, they don’t come as instructions on a form. They show up as assumptions we carry around without even noticing.

That we’re too old for bikinis. That we should trade high heels for practical shoes with good arch support. That staying up late is no longer a responsible choice.

That if we are lucky enough to have a good job and a wonderful family, we shouldn’t be googling “wine retreats in Tuscany.” We should simply be grateful for what we already have.

That this is the point in life when we’re meant to fade quietly into the background. That we shouldn’t be “too much.” Too loud. Too opinionated. Too excited. Posting too many selfies.

But the silliest rules aren’t really about shoes or bedtimes. The deeper rule is this: that we’re not supposed to want more anymore.

More fun.
More adventure.
More reinvention.
More visibility.
More joy.

That competence should matter more than curiosity. That it’s safer to keep playing the instrument we already know than risk sounding like a dying cat while we learn something new.

These are rules I have no problem breaking.

I’ve spent enough years being sensible.

If there’s a blank space on the form now, I’m writing down exactly what I want.

Maybe midlife isn’t about breaking all the rules. Maybe it’s about noticing which ones we never needed to follow in the first place. About putting down the instruments we didn’t choose and giving ourselves permission to start again — even if it sounds messy at first.

Some rules keep us safe.
Some rules keep us small.

Midlife is when we finally learn the difference.